If you’re looking for a charming New England town with great food, river views, and local flavor, I always say—don’t skip Middletown, Connecticut. I’ve explored its downtown, walked its riverside paths, and sampled meals that honestly caught me by surprise. It’s one of those places where college town energy (thanks to Wesleyan University) meets small-town friendliness—and I think you’ll feel that mix the moment you arrive.
Since it's a 2+ hour drive from NYC, I recommend spending the night so that you are not rushing.
Top Things to Do in Middletown, Connecticut
- Stroll along the Connecticut River at Harbor Park – I’ve taken peaceful walks here and even caught a boat tour or two. The views are beautiful, especially in the fall when the leaves are glowing.
- Explore Main Street – I always make time for downtown Middletown. You’ll find independent shops, great coffee spots, and a food scene that punches well above its weight. I’ve had amazing sushi, Indian food, and craft cocktails—all within a few blocks.
- Visit Wadsworth Falls State Park – I’ve hiked the trails here and cooled off by the falls in summer. It’s a quiet, easy escape into nature just minutes from town.
- Tour Wesleyan University – Whether I’m walking the leafy campus or popping into the art galleries and theaters, Wesleyan always feels lively and inspiring. You’ll sense the creativity everywhere.
- Catch a show at The Buttonwood Tree Performing Arts Center – I love this spot for music, storytelling, and open mic nights. It’s small, intimate, and full of local heart.
- Visit Kidcity Children’s Museum – When I’ve had little ones in tow, this place is a lifesaver. It’s playful, hands-on, and made just for kids to explore and imagine.
Best Time to Visit Middletown, CT
In my experience, spring and fall (April–June and September–October) are the most beautiful times to visit. The weather is perfect for outdoor walks and café hopping, and the fall foliage is truly something else. Summer has a relaxed vibe, and you’ll find live music and riverfront events. I’ve even visited in winter and found the downtown still cozy—especially with a warm bowl of ramen or coffee in hand.
How to Get to Middletown, CT
- By Car: I usually take Route 9 or I-91—it’s a scenic drive whether you’re coming from Hartford (about 30 minutes) or New Haven (about 40 minutes).
- By Train: There’s no direct train to Middletown, but I’ve taken Amtrak or Metro-North to New Haven or Meriden, then grabbed a rideshare or rental car. It’s a smooth connection.
- By Air: Bradley International Airport (BDL) near Hartford is the closest major airport. I’ve flown in and out of there and found it easy to navigate, just under an hour’s drive away.
Where to Stay in Middletown, CT
- Inn at Middletown – I’ve stayed here and loved the classic charm. It’s in the heart of downtown, walking distance to everything, with cozy rooms and a welcoming vibe.
- Airbnb Options – I’ve found some lovely local homes and apartments to rent, especially near Wesleyan or tucked into quiet residential streets. Great if you want a more personal, homey stay.
- Nearby Hotels in Cromwell or Meriden – If you’re looking for chain hotels with extra space or easy highway access, I’ve stayed just a few minutes outside Middletown and still been close to everything.
Best Things to Do in Middletown, CT
Kidcity Children's Museum - Let kids play and explore imaginative exhibits on a fun, hands-on family trip.
Wadsworth Falls State Park - Hike wooded trails and see scenic waterfalls on an easy spring outing.
Wesleyan University - Stroll the historic campus and admire classic architecture on a quiet retirement visit.
Empower Leadership Sports & Adventure Center - Zipline through trees and tackle obstacle courses on an exciting weekend adventure.
General Mansfield House - Tour preserved rooms and discover local history on an affordable cultural trip.
Van Vleck Observatory - Look at the stars and explore astronomy exhibits on an unusual kids outing.
Artfarm - Enjoy live performances and explore creative workshops on a summer arts-focused trip.
Dart Island State Park - Paddle the Connecticut River and relax onshore during a peaceful couples escape.
Taino Smokehouse - Savor smoky barbecue and enjoy bold flavors on a quick, affordable food stop.
In Summary...
(and if you want to revisit my photo journey)